KR950701921A - 피리딘 화합물 및 이의 제약학적 용도(pyridine compound and medicinal use thereof) - Google Patents
피리딘 화합물 및 이의 제약학적 용도(pyridine compound and medicinal use thereof)Info
- Publication number
- KR950701921A KR950701921A KR1019940704387A KR19940704387A KR950701921A KR 950701921 A KR950701921 A KR 950701921A KR 1019940704387 A KR1019940704387 A KR 1019940704387A KR 19940704387 A KR19940704387 A KR 19940704387A KR 950701921 A KR950701921 A KR 950701921A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- pyridyl
- methylthio
- optionally substituted
- hydrogen
- Prior art date
Links
- -1 Pyridine Compound Chemical class 0.000 title claims abstract 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
- 239000001257 hydrogen Substances 0.000 claims abstract 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims 4
- HEZSBUNWERXKSX-UHFFFAOYSA-N 1-methylsulfanylbenzimidazole Chemical compound C1=CC=C2N(SC)C=NC2=C1 HEZSBUNWERXKSX-UHFFFAOYSA-N 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- QGFLMCGANDTUTP-UHFFFAOYSA-N 2-[2-[2-(1h-imidazo[4,5-b]pyridin-2-ylsulfanylmethyl)-3-methylpyridin-4-yl]sulfanylethyl]-3,4-dihydro-1h-isoquinoline Chemical compound C1CC2=CC=CC=C2CN1CCSC1=CC=NC(CSC=2NC3=CC=CN=C3N=2)=C1C QGFLMCGANDTUTP-UHFFFAOYSA-N 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- QRUGBSZXSGYKAL-UHFFFAOYSA-N CC=1C(=NC=CC1SCCN1CCOCC1)C1=NC2=C(N1SC)C=CC=C2 Chemical compound CC=1C(=NC=CC1SCCN1CCOCC1)C1=NC2=C(N1SC)C=CC=C2 QRUGBSZXSGYKAL-UHFFFAOYSA-N 0.000 claims 1
- VCKUIDPEOOHIOT-UHFFFAOYSA-N CC=1C(=NC=CC1SCCNC(C)=O)C1=NC2=C(N1SC)C=CC=C2 Chemical compound CC=1C(=NC=CC1SCCNC(C)=O)C1=NC2=C(N1SC)C=CC=C2 VCKUIDPEOOHIOT-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 241000589989 Helicobacter Species 0.000 claims 1
- REIUUNLDDQXYPP-UHFFFAOYSA-N N-benzyl-N-methyl-2-[3-methyl-2-(1-methylsulfanylbenzimidazol-2-yl)pyridin-4-yl]sulfanylethanamine Chemical compound C(C1=CC=CC=C1)N(C)CCSC1=C(C(=NC=C1)C1=NC2=C(N1SC)C=CC=C2)C REIUUNLDDQXYPP-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract 2
- 241000590002 Helicobacter pylori Species 0.000 abstract 1
- 208000025865 Ulcer Diseases 0.000 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 230000000767 anti-ulcer Effects 0.000 abstract 1
- 230000002496 gastric effect Effects 0.000 abstract 1
- 229940037467 helicobacter pylori Drugs 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 231100000397 ulcer Toxicity 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
하기 구조식(Ⅰ)의 피리딘 화합물 및 제약학적으로 허용가능한 그의 염은 헬리코박터 필로리에 대한 항균 활성, 항궤양 활성, 위장 세포 보호 활성, 궤양 재발 방지 활성등을 가져서 제약학적 제제로서 유용하다.
〔상기식에서, R1은 수소 할로겐, 알킬, 알콕시등이고, R2및 R3각각 수소, 할로겐 또는 알킬이고, -P=Q-는 -C=CH-, -N=CH- 또는 -CH=N-이고, A는 산소원자, 황원자 또는 N(R4)(여기에서, R4는 수소, 알킬등이다)이고, n은 0,1 또는 2이고, B는 산소원자, S(0)p(p는 0, 1또는 2이다), 또는 N(R5) (R5는 수소 또는 알킬이다)이고, D는 단일결합, 알킬렌등이고, E는 알콕시알킬, -N(R6)(R7)이다〕.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 하기 구조식(Ⅰ)의 피리딘 화합물 또는 제약학적으로 허용가능한 그의 염 :상기식에서, R1은 수소, 할로겐, 알킬, 알콕시, 히드록실, 알콕시카르보닐, 카르복실, 할로알킬, 니트로, 아미노, 모노 -또는 디알킬아미노, 알콕시카르보닐 알킬아미노 또는 카르복시알킬아미노이고, R2및 R3는 동일하거나 상이하고, 각각 수소, 할로겐 또는 알킬이고. -P=Q-는 -CH=CH-, -N=CH-또는 -CH=N-이고, A는 산소원자, 황원자 또는 N(R4)(여기에서, R4는 수소, 알킬, 알콕시카르보닐, 히드록시알킬, 알콕시알킬, 아실옥시알킬, 알콕시카르보닐알킬, 카르복시알킬, 카르바모일, 카르바모일알킬, 모노 -또는 디알킬카르바모일, 모노 -또는 디알킬카르바모일알킬, 티오카르바모일, 또는 모노 -또는 디알킬티오카르바모일이다)이고, n은 0, 1또는 2이고, B는 산소원자, S(0)p(p는 0, 1또는 2이다), 또는 N(R5)(R5는 수소 또는 알킬이다)이고, D는 단일결합, 알킬렌, 치환기를 갖는 알킬렌 또는 옥소를 갖는 알킬렌이고, E는 알콕시알킬, 하기 구조식(a)(상기식에서, R6및 R7은 동일하거나 상이하고 각각 수소, 알킬, 시클로알킬, 아실, 알콕시카르보, 카르바모일, 모노 -또는 디알킬카르바모일, 임의적으로 치환된 페닐카르바모일, 티오카르바모일, 모노 -또는 디알킬티오카르바모일, 임의적으로 치환된 페닐티오카르바모일, 히드록시알킬, 알콕시카르보닐알킬, 임의적으로 치환된 페닐알킬카르바모일, 임의적으로 치환된 페닐알킬티오카르바모일, 카르복시알킬, 임의적으로 치환된 페닐, 임의적으로 치환된 페닐알킬 또는 임의적으로 치환된 헤테로아릴알킬이거나, R6및 R7은 인접한 질소원자와 함께 임의적으로 축합되고 임의적으로 치환된 복소환 고리를 형성할 수 있다)의 기, 또는 하기 구조식(b)(상기 식에서, R8은 수소, 알킬, 아실, 카르복시알킬 또는 임의적으로 치환된 페닐알킬이고, Y는 메틸렌, 산소원자 또는 황원자이고 1 및 m은 동일하거나 상이하고 각각 0 또는 1-3의 정수이다)의 기이며; 단, -P=Q-가 -CH=CH-이고 A는 N(R4)일때, 하기한 사항중 하나가 적용된다; (1) R4가 수소일때, B는 S(0)p(p는 0, 1 또는 2이다) 또는 N(R5)(R5는 수소 또는 알킬이다)이고; (2) R4가 카르바모일 또는 모노- 또는 디알킬카르바모일이고, B는 산소원자이고, D는 알킬렌이고 E는 알콕시일때, D는 탄소수 3 내지 10의 알킬렌이고; (3) R4가 카르바모일 또는 모노- 또는 디알킬카르바모일이고, B는 산소원자이고, D는 알킬렌이고 E는 구조식 (a)의 기일때, D는 탄소수 5 내지 10의 알킬렌이고 또는 구조식 (a)에서 R6및 R7은 동일하거나 상이하며 각각은 수소, 탄소수 3 내지 20의 알킬기, 시클로알킬, 아실, 임의적으로 치환된 페닐, 임의적으로 치환된 페닐알킬 또는 임의적으로 치환된 헤테로아릴알킬이거나, R6및 R7은 인접한 질소원자와 함께, 임의적으로 축합되고 임의적으로 치환된 복소환고리를 형성할 수 있으며; (4) R4가 탄소수 1 내지 6의 알킬 또는 탄소수 2 내지 7의 알콕시카르보닐이고, D는 알킬렌이고 E는 알콕시일때, B는 S(0)p(p는 0, 1또는 2이다) 또는 N(R5)(R5는 수소 또는 알킬이다)이다.〕
- 제1항에 있어서, B가 S(0)p(p는 0, 1또는 2이다)이고 기타 부호는 제1항에 정의한 바와같은 구조식(Ⅰ)을 갖는 피리딘 화합물 또는 제약학적으로 허용가능한 그의 염.
- 제1항에 있어서, 2-(3-메틸-4-(2-모르폴리노에틸티오)-2-피리딜)메틸티오- 1H-벤즈이미다졸, 2-(3-메틸-4-(2-(1,2,3,4-테트라히드로이소퀴놀린-2-일)에틸티오)-2-피리딜)메틸티오-1H-벤즈이미다졸, 2-(4-(2-(N-벤질-N-메틸아미노)에틸티오) -3-메틸-2-피리딜)메틸티오-1H-벤즈이미다졸, 2-(4-(1-벤질-4-퍼페리딜)티오-3-메 틸-2-피리딜)메틸티오-1H-벤즈이미다졸, 2-((3-메틸-4-(2-(1,2,3,4-테트라히드로이소퀴놀린-2-일)에틸티오)-2-피리딜)메틸티오)이미다조〔5,4-b〕피리딘, 에틸 2-(3-메틸-4-(2-모르폴리노에틸티오)-2-피리딜)메틸티오-1H-벤즈이미다졸-1-카르복실레이트, 메틸 2-(3-메틸-4-(2-(1,2,3,4-테트라히드로이소퀴놀린-2-일)에틸티오)-2-피 리딜)메틸티오-1H-벤즈이미다졸-1-카르복실레이트, 4-(2-((2-(1H-벤즈이미다졸-2-일)티오메틸-3-메틸-4-피리딜)티오)에틸)모르폴린 N-옥사이드, 2-(3-메틸-4-(2-아세틸아미노에틸티오)-2-피리딜)메틸티오-1H-벤즈이미다졸 2-(3-메틸-4-(2-벤질아미노에틸티오)-2-피리딜)메틸티오-1H-벤즈이미다졸-2-(3-메틸-4-(2-(2-히드록시에틸 아미노)에틸티오)-2-피리딜)메틸티오-1H-벤즈이미다졸 2-(3-메틸-4-(2-(N,N-디(2-히드록시에틸)아미노)에틸티오)2-피리딜)메틸티오-1H-벤즈이미다졸 2-(3-메틸-4- (2-(2-카르복시에틸아미노)에틸티오)-2-피리딜)메틸티오-1H-벤즈이미다졸 및 2- (3-메틸-4-(2-모르폴리노-2-카르복시에틸티오)-2-피리딜)메틸티오-1H-벤즈이미다졸로 구성된 군으로부터 선택되는 피리딘 화합물 또는 제약학적으로 허용가능한 그의 염.
- 제1항의 화합물 및 제약학적 첨가제를 포함하는 제약학적 조성물.
- 제1항의 화합물을 활성 성분으로서 포함하는 헬리코박터 속에 속하는 세균에 의해 야기된 여러 질병의 예방 또는 치료용 제제.
- 제1항의 화합물을 활성 성분으로서 포함하는 위장 질병의 예방 또는 치료용 제제.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16701792 | 1992-06-01 | ||
| JP92-167017 | 1992-06-01 | ||
| PCT/JP1993/000732 WO1993024480A1 (en) | 1992-06-01 | 1993-05-31 | Pyridine compound and medicinal use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR950701921A true KR950701921A (ko) | 1995-05-17 |
Family
ID=15841847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019940704387A KR950701921A (ko) | 1992-06-01 | 1993-05-31 | 피리딘 화합물 및 이의 제약학적 용도(pyridine compound and medicinal use thereof) |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0644191A1 (ko) |
| KR (1) | KR950701921A (ko) |
| CA (1) | CA2136993A1 (ko) |
| WO (1) | WO1993024480A1 (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0729957A4 (en) * | 1993-10-29 | 1996-12-27 | Yoshitomi Pharmaceutical | PYRIDINE COMPOUND AND ITS USE AS A REMEDY |
| PT731801E (pt) * | 1993-12-01 | 2002-04-29 | Byk Gulden Lomberg Chem Fab | Aminoalquilaminopiridinas substituidas |
| HUT76054A (en) * | 1994-06-10 | 1997-06-30 | Byk Gulden Lomberg Chem Fab | Thiopyridines, pharmaceutical compositions containing them, process for producing them and their use in the control of helicobacter bacteria |
| US5859030A (en) * | 1994-06-10 | 1999-01-12 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Substituted arylalkylthioalkylthiopyridines for use in the control of helicobacter bacteria |
| WO1996000224A1 (de) * | 1994-06-23 | 1996-01-04 | Byk Gulden Lomberg Chemische Fabrik Gmbh | 4-s- und n-substituierte 6-alkylpyridine zur bekämpfung von helicobacter-bakterien |
| EP0772611A1 (de) * | 1994-07-20 | 1997-05-14 | Byk Gulden Lomberg Chemische Fabrik GmbH | Piperazinothiopyridine zur bekämpfung von helicobacter-bakterien |
| JPH08133971A (ja) * | 1994-09-16 | 1996-05-28 | Toyama Chem Co Ltd | 抗ヘリコバクター剤 |
| AU3993595A (en) * | 1994-12-02 | 1996-06-19 | Takeda Chemical Industries Ltd. | Condensed imidazole derivatives, their preparation and use |
| US6914068B2 (en) | 2001-07-12 | 2005-07-05 | Basf Aktiengesellschaft | Thiazolo[4,5-b]pyridines as fungicides |
| BRPI0514611A (pt) * | 2004-08-26 | 2008-06-17 | Actelion Pharmaceuticals Ltd | uso de um composto, compostos, e, medicamento |
| CN100364989C (zh) * | 2004-09-30 | 2008-01-30 | 江苏豪森药业股份有限公司 | 拉唑类衍生物及其盐和用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL66340A (en) * | 1981-08-13 | 1986-08-31 | Haessle Ab | Pharmaceutical compositions comprising pyridylmethyl-thiobenzimidazole derivatives,certain such novel derivatives and their preparation |
| SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
| JPH0674272B2 (ja) * | 1986-11-13 | 1994-09-21 | エーザイ株式会社 | ピリジン誘導体及びそれを含有する潰瘍治療剤 |
| WO1992012976A1 (en) * | 1991-01-16 | 1992-08-06 | Yoshitomi Pharmaceutical Industries, Ltd. | Use of pyridine compound as selective drug and novel pyridine compound |
| WO1993006097A1 (en) * | 1991-09-20 | 1993-04-01 | Merck & Co., Inc. | Novel process for the preparation of anti-ulcer agents |
-
1993
- 1993-05-31 CA CA002136993A patent/CA2136993A1/en not_active Abandoned
- 1993-05-31 EP EP93910422A patent/EP0644191A1/en not_active Withdrawn
- 1993-05-31 KR KR1019940704387A patent/KR950701921A/ko active IP Right Grant
- 1993-05-31 WO PCT/JP1993/000732 patent/WO1993024480A1/ja not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0644191A4 (ko) | 1995-04-12 |
| EP0644191A1 (en) | 1995-03-22 |
| WO1993024480A1 (en) | 1993-12-09 |
| CA2136993A1 (en) | 1993-12-09 |
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